'Whitey' Bulger imitates machine gun, talks about a killing in recorded jail visit

By Kristina Sgueglia, CNN

Updated 6:45 AM ET, Wed July 3, 2013

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Photos:Who's who in the James 'Whitey' Bulger case

James "Whitey" Bulger, the former head of Boston's Winter Hill Gang, evaded police for 16 years before his 2011 arrest with girlfriend Catherine Greig in Santa Monica, California. After a lengthy trial, Bulger, seen here in his booking photo from June 23, 2011, was found guilty on 31 of 32 counts -- including involvement in 11 murders. On November 14, 2013, Bulger was given two life sentences plus five years. Here's a look at some of the people tied to Bulger's life of crime:

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Photos:Who's who in the James 'Whitey' Bulger case

James "Whitey" Bulger, seen here in a 1984 FBI photo, spent nine years in federal prison before he climbed the ranks of the Winter Hill Gang -- the preeminent Irish-American crime syndicate in the Boston area -- in the early 1970s.

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Photos:Who's who in the James 'Whitey' Bulger case

According to prosecutors, Bulger's crew learned that a bookie named Richard Castucci was cooperating with the government, and John Martorano was sent to kill him. Castucci was shot in the head in December 1976 and stuffed in a sleeping bag in the back of his car.

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Photos:Who's who in the James 'Whitey' Bulger case

Steve "The Rifleman" Flemmi, left, and bookie Dick O'Brien in one of several surveillance photographs entered into evidence in the Bulger trial. Flemmi, Bulger's partner, would meet O'Brien to collect thousands of dollars in "rent" every month.

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Photos:Who's who in the James 'Whitey' Bulger case

Bulger is accused of murdering Flemmi's stepdaughter, Deborah Hussey, in 1985 because she became a liability.

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Photos:Who's who in the James 'Whitey' Bulger case

Flemmi met Debra Davis at a jewelry store, and the couple dated for more than seven years. In 1981, Bulger is said to have killed Davis because she knew that Flemmi was an informant.

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Photos:Who's who in the James 'Whitey' Bulger case

Dr. Ann Marie Mires, a Massachusetts state forensic anthropologist, was brought in to Bulger's trial to show photos of his alleged victims, including Debra Davis. Because Davis' body was put into bags, almost all of her remains were recovered. Even some of her hair was preserved.

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Photos:Who's who in the James 'Whitey' Bulger case

Mug shots of Bulger in 1953, about a year after his honorable discharge from the U.S. Air Force.

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Photos:Who's who in the James 'Whitey' Bulger case

Bulger was the godfather to John Martorano's first son. Martorano has admitted to 20 killings as part of Boston's Winter Hill Gang and was the government's star witness against Bulger.

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Photos:Who's who in the James 'Whitey' Bulger case

In 2008, John Martorano, pictured here, testified against former FBI agent John Connolly, who was accused of leaking sensitive information about former gambling executive John Callahan. Martorano testified that he shot his friend Callahan on Bulger's orders in 1982.

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Photos:Who's who in the James 'Whitey' Bulger case

John Callahan was an organized crime associate of the Winter Hill Gang and former president of World Jai Alai. Prosecutors allege Bulger ordered a hit on Callahan after he learned he would be cooperating with the feds on the high-profile murder of an Oklahoma businessman, Roger Wheeler.

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Photos:Who's who in the James 'Whitey' Bulger case

Bulger is accused in the slaying of Wheeler, who was gunned down outside a country club in Oklahoma in 1981.

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Photos:Who's who in the James 'Whitey' Bulger case

Joe Notorangeli was gunned down by the Winter Hill gang in 1973, according to Martorano.

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Photos:Who's who in the James 'Whitey' Bulger case

John Connolly was convicted of second-degree murder in the slaying of Callahan and received a 40-year sentence in 2009. Connolly is appealing.

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Photos:Who's who in the James 'Whitey' Bulger case

Former FBI supervisor John Morris testified at Bulger's trial that he provided information to Bulger in exchange for money and gifts. Here, Morris testifies during the John Connolly murder trial in Miami in 2008.

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Photos:Who's who in the James 'Whitey' Bulger case

Bulger's girlfriend, Catherine Greig, was sentenced to eight years in federal prison in 2012 for identity fraud and helping the reputed mob boss avoid capture for 16 years.

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Photos:Who's who in the James 'Whitey' Bulger case

J.W. Carney, Bulger's defense attorney, arrives at the U.S. Federal Courthouse for the start of Bulger's trial in Boston on Wednesday, June 12, 2013.

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Photos:Who's who in the James 'Whitey' Bulger case

This undated surveillance photo released by the U.S. Attorney's Office in Boston shows Bulger, left, with his former right-hand man, Kevin Weeks. Weeks took the witness stand at Bulger's racketeering trial and described a double slaying, multiple extortions and drug dealing.

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Photos:Who's who in the James 'Whitey' Bulger case

Bulger and Kevin Weeks walk around Castle Island on Boston Harbor.

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Photos:Who's who in the James 'Whitey' Bulger case

Kevin Weeks leaves the courthouse in July 2013 after testifying in graphic detail about how Bulger killed Arthur "Bucky" Barrett, Joey McIntyre and Deborah Hussey.

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Photos:Who's who in the James 'Whitey' Bulger case

The remains of Thomas King, former member of the Winter Hill Gang, were found in late 2000 and included these driving gloves, a bulletproof vest, a navy suit, and a claddagh ring. Martorano, one of Bulger's hitmen, testified that he himself had shot King in the back of the head.

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Photos:Who's who in the James 'Whitey' Bulger case

Stephen Rakes, 59, was scheduled to be a witness for the prosecution before he was dropped from the list. His body was found July 17, 2013, in Lincoln, Massachusetts, west of Boston. Rakes' business associate has been charged with his murder. Authorities said Rakes' killing was unrelated to the Bulger case.

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Photos:Who's who in the James 'Whitey' Bulger case

Trying to show a softer, lighter side of Bulger, his defense lawyers released numerous photos of their client during the 2013 trial. The tactic didn't work: Bulger will spend the rest of his life in prison.

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Story highlights

Recordings of James "Whitey" Bulger's jail visits are played in court

Bulger talks about one shooting of which he is accused, but doesn't incriminate himself

Witness who says he paid Bulger a cut of drug sales captivates courtroom with testimony

A federal jury on Tuesday heard the voice of reputed Boston mob boss James "Whitey" Bulger in conversations recorded during visits by his family members since his incarceration in 2011.

Bulger, who had only been heard uttering choice expletives and inappropriate laughter during trial so far, can be heard imitating a machine gun while describing the death of a Dorchester bartender, who he is charged with killing along with 18 others.

"Bull Dog's was uh -- Eddie Connors ... the guy in the phone booth ... pa pa pa pa pow," Bulger says, laughing with his niece and nephew, the son and daughter of hisbrother William Bulger, who was president of the Massachusetts State Senate for 17 years.

Prosecutors allege Bulger killed Connors in a phone booth in 1975 for running his mouth about Bulger and his "Winter Hill Gang" killing another Charlestown gangster.

Karen Smith, who testified earlier about the last time she saw Connors, her father -- who she said used to come home for dinner and put her and her brother to bed every night -- was sobbing in her seat in the courtroom when the audio was played.

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Bulger did not implicate himself as the killer in the partially transcribed phone conversation of a visit on October 13, 2012. He said, "They threw my name in the mix," likely referring to others placing the blame on him. "As usual," his nephew responded. "But that is what happened," Bulger said to his niece and nephew.

In another audio recording, Bulger described a run-in with potential robbers at the liquor store he and his partners allegedly used as an "office."

"So I picked up a shotgun and I'm aimin' it at them and the guy looked up and oh...," Bulger said to his brother John Bulger.

"And I put one in the chamber like, ptwwww -- and he looked up and I'm aimin' and he says to the other guy, he says, 'Hey, (Bulger laughs) a bag of peanuts please.' "

"We were lucky they didn't try to do nothing," Bulger told his brother during this December 11, 2012, visit.

The prosecution has been trying to prove Bulger is guilty of 19 murder charges, as well as extortion, racketeering and money laundering. Bulger, 83, has pleaded not guilty. The trial entered its 15th day Tuesday, and will resume Monday after a long holiday weekend. The prosecution has called more than 30 witnesses and could call as many as 80 before the defense is given an opportunity to make its case. Judge Denise Casper advised jurors on Tuesday that court is likely to go into September.

William "Billy" Shea was also called to the stand.

Shea said he sold drugs for Bulger and gave him a "chop," or piece of the profit, during the reign of Bulger's South Boston empire, which prosecutor's say lasted nearly 20 years. Shea also described how he and Bulger cultivated a friendship and a business together, often pointing to "Jim," and referring to him during his storytelling, as if they were telling it together.

At one point, Shea was asked to describe how much money he was making at the height of his drug selling, when he was paying Bulger a cut of $4,000 a week. "It was brisk, a good weekly take. I would say plus 100-thousand or more every week. I'm thinking Jim's looking at me saying this son of a bitch got that much money and I only got that end ... I don't know!" Bulger laughed, as did the courtroom.

Shea said he sold "gangster" weed and later partnered with Joseph Tower to sell cocaine. The jury, and the courtroom, appeared captivated by his storytelling.

When Shea was asked to identify Bulger, he pointed at him and said, "He is that young fella right there," and Bulger returned his old friend's smile.

Shea, like the other associates, painted Bulger as their insurance, the "protection" they needed to do business and not be bothered. Both Tower and Shea have testified that Bulger helped them when they most needed it. Tower said Bulger saved his brother's life. Tower said Tuesday, "Bulger was well known and well feared -- If you were with Mr. Bulger you could operate, you didn't need the police." Both Shea and Tower are testifying under immunity agreements with the federal government.

Shea told the jury that Bulger got upset with him when Shea indicated he wanted to leave the business. When Shea said he began reconciling with his old friend, it was as if no one was in the courtroom but the two of them.

"It was the first time you ever threatened me. I am sure you remember it. I do. You said, 'You remember what happened to Bucky Barrett?' I understood it to be what it meant. Bucky Barrett is someone who is missing. I took it as a threat," Shea said to Bulger, who was sitting no more than five feet in front of him. Bulger is charged with the murder of Arthur "Bucky" Barrett after allegedly shaking him down for money after a bank robbery.

Then it seemed Shea remembered he was in court and said, "It changed my perception of Jim just like that. I am looking at a guy who I thought I knew for many years, and he is saying you will do what I say or I'll whack you, basically."

Shea said shortly after that, Bulger and his associates picked Shea up and took him to the South Boston projects, where Bulger led him into a cellar to "frighten me or whack me." Shea said Bulger just wanted to talk about "trust." Shea said he had his back to the concrete on the lookout for the associates, who he thought were going to come down the steps to the cellar and "make" him. Shea said Bulger was also questioning him about "skimming" the drugs to set up a side business, but Shea said he "hadn't seen the product in years," adding "that's what Jim taught me, to always have buffers."

Shea said about Bulger, "I have always feared him a little bit because I know he's smart and clever. I am thinking if he makes a move..." and then Shea looked at Bulger. "You make a move, you are going with me, Jim. That's what was going through my head."

Shea said Bulger didn't want any loose ends, and Shea assured him he didn't rat out Bulger when he was arrested in 1983 on drug trafficking charges, and he wasn't going to do it once he backed out of the business. The men finished their conversation and Bulger offered Shea a ride home, but Shea opted to walk, he said.

Shea was with his 4-year-old son when he bumped into Bulger on a snowy night a month later. Shea said Bulger immediately told him, "Bill, we are just here by chance," in an effort to ease his nerves. Shea said he hadn't seen Bulger since then until Tuesday.